(3R,2'R)-3-quinuclidinyl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: (3R,2'R)-3-quinuclidinyl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate
• 英文别名: HL-031120；(2R)-2-Cyclopentyl-2-hydroxy-2-phenylacetic Acid (3R)-1-azabicyclo[2.2.2]oct-3-yl Ester；(R)-cyclopentyl-hydroxy-phenyl-acetic acid (R)-1-aza-bicyclo[2.2.2]oct-3-yl ester；[(3R)-1-azabicyclo[2.2.2]octan-3-yl] (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: RFXCNPOWSCFJCD-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-扁桃酸 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氯化亚砜 、 三氟甲磺酸 、 氢气 、 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 正庚烷 、 水 、 正戊烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 30.5h， 生成 (3R,2'R)-3-quinuclidinyl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate
  参考文献：
  名称：

  Stereoselective Synthesis of the Optical Isomers of a New Muscarinic Receptor Antagonist, HL‐031120

  摘要：

  We present here a practical stereoselective synthetic method to produce enantiopure isomers of a new muscarinic receptor antagonist, HL-031120 (3-quinuclidinyl-2'-cyclopentyl-2'-hydroxy-2'-phenylacetate, I). Four optical isomers were effectively by stereoselective synthesized using pivaldehyde as steric hindrance agent from the chiral starting material, (S) or (R)- mandelic acid. The isomers were obtained with 70-76% yields in 98-99% e. e.

  DOI：

  10.1080/00397910600602453

文献信息

• US7879874B2
  申请人：——

  公开号：US7879874B2

  公开（公告）日：2011-02-01
• US7893087B2
  申请人：——

  公开号：US7893087B2

  公开（公告）日：2011-02-22
• Stereoselective Synthesis of the Optical Isomers of a New Muscarinic Receptor Antagonist, HL‐031120
  作者：Yu‐Min Liu、He Liu、Bo‐Hua Zhong、Ke‐Liang Liu

  DOI：10.1080/00397910600602453

  日期：2006.7

  We present here a practical stereoselective synthetic method to produce enantiopure isomers of a new muscarinic receptor antagonist, HL-031120 (3-quinuclidinyl-2'-cyclopentyl-2'-hydroxy-2'-phenylacetate, I). Four optical isomers were effectively by stereoselective synthesized using pivaldehyde as steric hindrance agent from the chiral starting material, (S) or (R)- mandelic acid. The isomers were obtained with 70-76% yields in 98-99% e. e.